In this chapter I examine the experiences of parole in South Australia. Specifically, I explore three dimensions: 1) how (would-be) parolees try to take charge of their post-custodial circumstances in order to avoid being “set up to fail”; 2) how over-policing (and outright police harassment) can inhibit successful integration into the community; and 3) how the right “type” of parole officer can make a positive difference even in the most difficult situations. In concluding I suggest that in political climates governed by a heightened emphasis on risk management, the capacity to build therapeutic and productive relationships with clients is largely pushed out of the frame. Implications for successful reintegration are briefly discussed.